Inside Barron And Tessa Hilton's Relationship

The Hilton family added a new member to its dynasty in 2018 when Barron and Tessa Hilton tied the knot. After stealing headlines with news of their fairytale romance, Barron and Tessa have built a loving relationship and family largely shielded from the spotlight. Barron's older sisters Paris Hilton and Nicky Hilton Rothschild have had their fair share of time basking in the glow of the spotlight, and even the family matriarch Kathy Hilton has reached stardom on reality TV. However, Barron, for the most part, has avoided scrutiny from the press.

Aside from some brushes with the law in his teens, Barron mostly stayed out of the public gaze, with a few appearances on red carpets and posts to his now-defunct foodie Instagram, Barron's Bites. Meanwhile, Tessa Gräfin von Walderdorff, a German countess and socialite, wrapped up her degree at Bard College and moved on to an internship at the New York marketing firm Laird and Partners.

Sparks flew when Barron met the glamorous Tessa at a restaurant in the Caribbean during a vacation in 2016. One whirlwind romance, a lavish destination wedding, and a growing family later, Barron and Tessa have become quite the household. Here are just a few of the couple's relationship highlights over the years.

While vacationing in Saint Barthélemy in 2016, Barron and Tessa Hilton crossed paths at a popular cabaret bar and restaurant, only a few days after the New Year. The small Caribbean island had been the go-to Walderdorff family vacation destination since Tessa was a child. Unsurprisingly, the Hilton family's hotel empire also extends to St. Barts' sunny beaches, from modest hotels to upscale villas and resorts bordering the luxury beaches of the island.

Despite the heavy Hilton presence, Tessa had no way of knowing that the island would also be the place she'd meet her future husband — or that she was destined to join the Hilton clan. "Laying eyes on Barron for the first time was so surreal, almost like a dream," Tessa revealed to Spirit and Flesh. "He was sitting there, next to me, and it was as if someone had all of a sudden pressed 'mute' on the remote control to silence the movie around us." Pressing mute on the raucous party atmosphere of Le Ti is no mean feat, even for a couple like the Hiltons. Tessa and Barron knew from that moment that they shared a special connection. As Barron put it in a since-deleted Instagram caption, "It was just our second encounter, but she brought me this instant sense of security in a sea of familiar strangers" (via Hollywood Life).

Although their story would seem to be love at first sight, it took a bit longer for Barron and Tessa Hilton to fully establish themselves as the power couple they are now. The couple dated for some time before downgrading briefly to roommates and friends while they each traveled separately in the summer of 2017. After a month and a half apart, Tessa and Barron reunited in New York City and decided to make their relationship official.

Barron planned a private proposal on Coney Island in September that same year — a destination they had promised each other they'd visit together — and popped the question with a heartfelt handwritten letter on the Coney Island Ferris wheel. 

On the Ferris wheel's second rotation, Barron got down on one knee, proposing at the top with a pear-shaped diamond. Tessa, unsurprisingly, gave an enthusiastic "yes." The couple announced their engagement on Instagram with a casual photo of the couple sharing a kiss in Central Park.

Barron and Tessa Hilton married in a lavish ceremony in the Caribbean in 2018, on the island where they first met and fell in love. Mirroring Tessa's parents' wedding exactly 30 years earlier, the couple got hitched in an intimate ceremony in St. Barts. With the destruction of Hurricane Irma just in the rearview, the couple worried about finding the right venue for their big day. But they found themselves struck by a 19th-century Anglican church in the island's capital of Gustavia, and chose the yellow chapel for their ceremony, along with a beachfront villa owned by a friend of their wedding planner for their reception.

The couple married officially in a civil ceremony at Gustavia's town hall, capped with their church ceremony and wild reception two days later. After their small church ceremony and a few dreamy waterfront portraits, the couple celebrated with their family well into the night. The couple's first dance was to a song by American dream pop band Cigarettes After Sex. Barron's older sister Paris Hilton then kicked off the party, playing DJ for a portion of the night. Now that's hot!

As an offshoot of the hotel giant, Barron and Tessa Hilton launched Hilton Estates Group, an event production service for the particularly well-connected and well-heeled. The avant-garde event company was formed by the pair to bring attention to elite real estate properties that may not have potential buyers lining up. Using their stake in Casa Del Sol Tequila, the Hiltons spice up their events with signature tequila cocktails and high-end clientele in an effort to reel in top-tier real estate investors.

The company's launch event in 2022, dubbed the "Goddess Art Show," featured large pop art portraits with a DJ set spun by Kim Ann Foxman, as well as a performance from singer Paris Jackson. The real star, of course, was the event's setting — a spacious mansion just down the road from the former Beverly Hills home of President and First Lady Ronald and Nancy Reagan. 300 guests attended the initial launch with a few familiar faces, including Barron's sister Paris Hilton. The event generated buzz for both the property and for the couple's event planning prowess, leading them to throw three more events at languishing properties over the course of 2022, including an event featuring the musical stylings of Rainey Qualley and a daring food choice — champagne glasses filled with rotisserie chicken nuggets. 

Barron and Tessa Hilton have played all the roles a couple could play together: friends, partners in life, and business partners. Barron began working as a Senior Vice President at one of the family businesses, Hilton & Hyland, a luxury real estate agency catering to the wealthy and elite. Founded by Barron's father Richard Hilton with architectural historian Jeff Hyland in 1993, the business has long served Beverly Hills as a preferred real estate agency.

Shortly before their marriage in 2018, Tessa studied and received her real estate license, joining her fiancé on Hilton & Hyland's team of luxury property brokers. Barron and Tessa both have given social media space to some of the most prized homes in their rotation, but Barron may have won the most coveted and sentimental of listings with his joint handling of his grandfather's palatial estate. Listed in 2020, Richard and Barron Hilton sold the historic Bel-Air mansion owned by William Barron Hilton in 2021 for the hefty price tag of $61.5 million. Though Richard and Barron both stepped away from the business in 2022, new collaborations between the Hilton family abound with the father-son duo forming their own brokerage, Hilton & Hilton.

The newest branch of the Hilton family had a big announcement in 2019 — Tessa and Barron Hilton were having a baby. To commemorate the occasion, Tessa's father, acclaimed artist and photographer, Franz Walderdorff, shot a moody series of photos of the couple for their maternity shoot. According to Walderdorff's artist biography accompanying some of his more recent work, the photographer's primary subject has always been beauty, whether that's in the most expected of places such as an "Allure" cover shoot or the most unexpected. Needless to say, beauty was not hard to find with Tessa's photo shoot. 

Although the couple weren't shy about sharing photos of Tessa's baby bump over the months before their child's birth, their maternity shoot was especially significant for Tessa. Remarking on the shoot in her Instagram post of the photos, she said, "The energy on set was powerful, full of emotion, raw and serene — a beautiful synergy between father, daughter, husband, and child.."

On March 11, 2020, Barron and Tessa Hilton welcomed the birth of their new daughter, Milou Alizee Hilton, a new member of both the hotel dynasty and the noble House of Walderdorff. The couple put their love of Saint Barthélemy front and center in their romance, and again with the birth of their daughter. Baby Milou was named after Pointe Milou, a district on the island where they met and married. As a residential neighborhood, Pointe Milou features views from the volcanic cliffs off into the bay from its luxe villas. It's also the very neighborhood where Barron and Tessa first met, at the swashbuckling pirate-themed tavern cabaret and local destination, Le Ti.

In a statement to People, Barron and Tessa expanded further on their name choice, adding, "Her middle name, Alizée, means 'trade winds' in French. The winds of the island are what brought us together and then a few years later, it is what brought us Milou. She is a gift from the island."

Just two years later, Barron and Tessa Hilton announced the birth of their second child, a son named Caspian Barron Hilton born September 4, 2022. Tessa shared pictures of their new son on Instagram a few days after his birth, featuring Tessa in the hospital and a picture of their toddler, Milou Alizee Hilton, kissing her new brother's head.

A month prior, the Hilton family celebrated the clan's newest scion with a posh pastel-themed baby shower at Kathy Hilton's Malibu home. Bucking more recent trends, the couple decided to forego a gender reveal, waiting until the birth to find out the baby's gender. Appropriately, Baby Caspian's baby shower was awash with both pinks and blues, with Tessa and Milou dressed in coordinating pink dresses for the occasion. 

Commenting to People on the pregnancy, the couple asserted their excitement. "It wasn't planned, but we've realized that the best things in life never are," Barron and Tessa admitted. Their announcement followed the birth of Barron's sister Nicky Hilton Rothschild and James Rothschild's son and preceded the birth announcement of Paris Hilton and Carter Reum's daughter via surrogate in January.

Almost exactly a year after the birth of Caspian Barron Hilton, Tessa Hilton announced her third pregnancy on Instagram with a set of family photos featuring their two children. In the pictures, Barron and Tessa Hilton share a kiss on the beach with their children, and Tessa's baby bump is on full display in a white dress and denim shirt. "Our third little angel is on the way!!" Tessa captioned her post. 

However, the couple soft-launched their pregnancy announcement the night before. Tessa's baby bump was unmistakable when she stepped on the red carpet for photos from the Zodiac Ball, a benefit event supporting the Children's Oncology Support Fund and co-chaired by Barron and Tessa. The couple posed with each of their hands over Tessa's visible baby bump, wearing coordinated black and silver outfits. Speaking to The Messenger at the event, Tessa joked, "There was no hiding the bump tonight!" She additionally revealed that the couple was expecting their second boy. "I was sure it was a little girl because of how good I'm feeling, but it is a boy," she said.